HU203559B - Process for producing 1-deoxy-nojirimicin derivatives and pharmaceutical compositions containing them as active components - Google Patents

Process for producing 1-deoxy-nojirimicin derivatives and pharmaceutical compositions containing them as active components Download PDF

Info

Publication number: HU203559B
Authority: HU; Hungary
Prior art keywords: deoxy; benzyl; tri; methyl; dideoxy
Prior art date: 1988-06-02

Application number

HU892791A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT50191A (en

Inventor

Jean-Bernard Ducep

Charles Danzin

Original Assignee

Merrell Dow Pharma

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-06-02

Filing date

1989-05-31

Publication date

1991-08-28

1989-05-31 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1989-12-28 Publication of HUT50191A publication Critical patent/HUT50191A/hu

1991-08-28 Publication of HU203559B publication Critical patent/HU203559B/hu

Links

238000000034 method Methods 0.000 title claims description 13
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
LXBIFEVIBLOUGU-JGWLITMVSA-N duvoglustat Chemical class OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O LXBIFEVIBLOUGU-JGWLITMVSA-N 0.000 title description 9
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 30
-1 xyosyl Chemical group 0.000 claims description 19
229960002920 sorbitol Drugs 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 14
125000003147 glycosyl group Chemical group 0.000 claims description 13
125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
238000010992 reflux Methods 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
125000000824 D-ribofuranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@]1([H])O[H] 0.000 claims description 2
125000003525 allosyl group Chemical group 0.000 claims description 2
125000003420 altrosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 2
125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
150000002243 furanoses Chemical class 0.000 claims description 2
125000001503 gulosyl group Chemical group C1([C@H](O)[C@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims description 2
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239000002253 acid Substances 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
125000003796 lyxosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 claims 1
150000003215 pyranoses Chemical class 0.000 claims 1
150000003839 salts Chemical class 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
230000002829 reductive effect Effects 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
239000000243 solution Substances 0.000 description 26
239000000203 mixture Substances 0.000 description 25
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239000012074 organic phase Substances 0.000 description 13
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
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239000008103 glucose Substances 0.000 description 7
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150000001299 aldehydes Chemical class 0.000 description 6
150000001412 amines Chemical group 0.000 description 6
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
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229920006395 saturated elastomer Polymers 0.000 description 6
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DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
206010012601 diabetes mellitus Diseases 0.000 description 5
201000010099 disease Diseases 0.000 description 5
239000006260 foam Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 5
LXBIFEVIBLOUGU-UHFFFAOYSA-N Deoxymannojirimycin Natural products OCC1NCC(O)C(O)C1O LXBIFEVIBLOUGU-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
238000003556 assay Methods 0.000 description 4
150000001720 carbohydrates Chemical class 0.000 description 4
235000014633 carbohydrates Nutrition 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
102000003886 Glycoproteins Human genes 0.000 description 3
108090000288 Glycoproteins Proteins 0.000 description 3
241000725303 Human immunodeficiency virus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
229910000085 borane Inorganic materials 0.000 description 3
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000000746 purification Methods 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
FLLFKFMTRYRALL-ARQDHWQXSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxy-n-methylhexanamide Chemical compound CNC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FLLFKFMTRYRALL-ARQDHWQXSA-N 0.000 description 2
JCZPMGDSEAFWDY-SQOUGZDYSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanamide Chemical compound NC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO JCZPMGDSEAFWDY-SQOUGZDYSA-N 0.000 description 2
208000030507 AIDS Diseases 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
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239000003810 Jones reagent Substances 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
238000007239 Wittig reaction Methods 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical group C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
239000007789 gas Substances 0.000 description 2
229930182470 glycoside Natural products 0.000 description 2
150000002338 glycosides Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000010166 immunofluorescence Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
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BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 2
229910001641 magnesium iodide Inorganic materials 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
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230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
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230000035484 reaction time Effects 0.000 description 2
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MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
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NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
239000012071 phase Substances 0.000 description 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical group CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003214 pyranose derivatives Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000001177 retroviral effect Effects 0.000 description 1
238000002976 reverse transcriptase assay Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
238000009901 transfer hydrogenation reaction Methods 0.000 description 1
ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
241001430294 unidentified retrovirus Species 0.000 description 1
230000005727 virus proliferation Effects 0.000 description 1
125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/048—Pyridine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/06—Heterocyclic radicals

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Diabetes (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Crystallography & Structural Chemistry (AREA)
Hematology (AREA)
Bioinformatics & Cheminformatics (AREA)
Obesity (AREA)
Virology (AREA)
Oncology (AREA)
Endocrinology (AREA)
Communicable Diseases (AREA)
Emergency Medicine (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Child & Adolescent Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Hydrogenated Pyridines (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

HU892791A 1988-06-02 1989-05-31 Process for producing 1-deoxy-nojirimicin derivatives and pharmaceutical compositions containing them as active components HU203559B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP88401340A EP0344383A1 (de)	1988-06-02	1988-06-02	Alpha-Glucosidase-Inhibitoren

Publications (2)

Publication Number	Publication Date
HUT50191A HUT50191A (en)	1989-12-28
HU203559B true HU203559B (en)	1991-08-28

Family

ID=8200392

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU892791A HU203559B (en)	1988-06-02	1989-05-31	Process for producing 1-deoxy-nojirimicin derivatives and pharmaceutical compositions containing them as active components

Country Status (22)

Country	Link
US (1)	US5157116A (de)
EP (1)	EP0344383A1 (de)
JP (1)	JP2791419B2 (de)
KR (1)	KR0155541B1 (de)
CN (1)	CN1023803C (de)
AR (1)	AR247890A1 (de)
AT (1)	ATE129716T1 (de)
AU (1)	AU608711B2 (de)
CA (1)	CA1339740C (de)
DE (1)	DE68924670T2 (de)
DK (1)	DK267489A (de)
ES (1)	ES2081857T3 (de)
FI (1)	FI92934C (de)
GR (1)	GR3018354T3 (de)
HU (1)	HU203559B (de)
IE (1)	IE68455B1 (de)
IL (1)	IL90463A0 (de)
NO (1)	NO170023C (de)
NZ (1)	NZ229337A (de)
PH (1)	PH25908A (de)
PT (1)	PT90713B (de)
ZA (1)	ZA894068B (de)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3936295A1 (de) *	1989-11-01	1991-05-02	Bayer Ag	Verfahren zur herstellung von zwischenprodukten und zur synthese von n-(2-hydroxyethyl)-2-hydroxymethyl-3,4,5-trihydroxypiperidine
US5504078A (en) *	1990-06-08	1996-04-02	Merrell Dow Pharmaceuticals Inc.	α-glucosidase inhibitors
US5844102A (en) *	1994-07-07	1998-12-01	University Of Maryland Baltimore County	Glycohydrolase inhibitors, their preparation and use thereof
JP3580900B2 (ja) *	1995-04-20	2004-10-27	ホクレン農業協同組合連合会	α−グルコシダーゼ阻害剤を含む糖を主体とする組成物を有効成分とする食品及び飼料
AU4335997A (en) *	1996-09-09	1998-03-26	Wisconsin Alumni Research Foundation	Human salivary proteins and fragments thereof having alpha-glucosidase inhibitory activity
GB2338235B (en) *	1997-04-15	2001-11-14	Csir	Appetite suppressing plant extracts
WO1998050359A1 (en) *	1997-05-06	1998-11-12	Novo Nordisk A/S	Novel heterocyclic compounds
GB2355657B (en) *	1999-10-27	2004-07-28	Phytopharm Plc	Inhibitors Of Gastric Acid Secretion
GB2363985B (en)	2000-06-30	2004-09-29	Phytopharm Plc	Extracts,compounds & pharmaceutical compositions having anti-diabetic activity and their use
JP4486792B2 (ja)	2003-06-12	2010-06-23	学校法人近畿大学	環状オニウム化合物およびグルコシダーゼ阻害剤
US7262318B2 (en) *	2004-03-10	2007-08-28	Pfizer, Inc.	Substituted heteroaryl- and phenylsulfamoyl compounds
WO2005092334A2 (en) *	2004-03-25	2005-10-06	David Priestman	Use of n-substituted imino sugars for appetite suppression
US20050288340A1 (en) *	2004-06-29	2005-12-29	Pfizer Inc	Substituted heteroaryl- and phenylsulfamoyl compounds
AP2007003979A0 (en) *	2004-11-23	2007-06-30	Warner Lambert Co	7-(2h-pyrazol-3-yl)-3,5-dihyroxy-heptanoic acid derivatives as hmg co-a reductase inhibitors for thetreatment of lipidemia
WO2006133447A1 (en) *	2005-06-08	2006-12-14	Amicus Therapeutics, Inc.	Crystalline sugar compositions and method of making
SI2027137T1 (sl) *	2005-06-08	2015-06-30	Amicus Therapeutics, Inc.	ÄŚiĹˇÄŤenje imino in amino sladkorja
CN101228173A (zh) *	2005-06-08	2008-07-23	阿米库斯治疗学公司	三氟甲磺酸酯化的化合物的稳定化
US7741317B2 (en)	2005-10-21	2010-06-22	Bristol-Myers Squibb Company	LXR modulators
US7888376B2 (en)	2005-11-23	2011-02-15	Bristol-Myers Squibb Company	Heterocyclic CETP inhibitors
GB0614947D0 (en) *	2006-07-27	2006-09-06	Isis Innovation	Epitope reduction therapy
CN101663262B (zh)	2006-12-01	2014-03-26	百时美施贵宝公司	用于治疗动脉粥样硬化和心血管疾病的作为cetp抑制剂的n-(3-苄基)-2,2-(二苯基)-丙-1胺衍生物
US8877717B2 (en)	2007-03-12	2014-11-04	Zadec Aps	Anti-diabetic extract of rooibos
US8969514B2 (en)	2007-06-04	2015-03-03	Synergy Pharmaceuticals, Inc.	Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
MX354786B (es)	2007-06-04	2018-03-21	Synergy Pharmaceuticals Inc	Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos.
ES2522968T3 (es)	2008-06-04	2014-11-19	Synergy Pharmaceuticals Inc.	Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos
AU2009270833B2 (en)	2008-07-16	2015-02-19	Bausch Health Ireland Limited	Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders
US20130072519A1 (en)	2010-05-21	2013-03-21	Edward Lee Conn	2-phenyl benzoylamides
WO2012027331A1 (en)	2010-08-27	2012-03-01	Ironwood Pharmaceuticals, Inc.	Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
EP2680874A2 (de)	2011-03-04	2014-01-08	Pfizer Inc	Edn3-ähnliche peptide und ihre verwendung
US20150050371A1 (en)	2012-03-09	2015-02-19	Biotropics Malaysia Berhad	Extract Formulations of Rhodamnia Cinerea And Uses Thereof
AU2014235215A1 (en)	2013-03-15	2015-10-01	Synergy Pharmaceuticals Inc.	Agonists of guanylate cyclase and their uses
AU2014235209B2 (en)	2013-03-15	2018-06-14	Bausch Health Ireland Limited	Guanylate cyclase receptor agonists combined with other drugs
EP2986599A1 (de)	2013-04-17	2016-02-24	Pfizer Inc.	N-piperidin-3-ylbenzamid-derivate zur behandlung von herz-kreislauf-erkrankungen
BR112015030326A2 (pt)	2013-06-05	2017-08-29	Synergy Pharmaceuticals Inc	Agonistas ultrapuros de guanilato ciclase c, método de fabricar e usar os mesmos
KR102431436B1 (ko)	2014-08-29	2022-08-10	테스 파마 에스.알.엘.	α-아미노-β-카복시뮤콘산 세미알데히드 데카복실라제의 억제제
WO2016055901A1 (en)	2014-10-08	2016-04-14	Pfizer Inc.	Substituted amide compounds
WO2018069532A1 (en)	2016-10-14	2018-04-19	Tes Pharma S.R.L.	Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase
AR117122A1 (es)	2018-11-20	2021-07-14	Tes Pharma S R L	INHIBIDORES DE LA ÁCIDO a-AMINO-b-CARBOXIMUCÓNICO SEMIALDEHÍDO DESCARBOXILASA
BR112021013807A2 (pt)	2019-01-18	2021-11-30	Astrazeneca Ab	Inibidores de pcsk9 e seus métodos de uso

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1555654A (en) *	1977-06-25	1979-11-14	Exxon Research Engineering Co	Agricultural burner apparatus
NO154918C (no) *	1977-08-27	1987-01-14	Bayer Ag	Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin.
DE2830469A1 (de) *	1978-07-11	1980-01-24	Bayer Ag	Herstellung von l-desoxy-nojirimycin und n-substituierten derivaten
DE2922760A1 (de) *	1979-06-05	1980-12-11	Bayer Ag	Neue derivate von 3,4,5-trihydroxypiperidin, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel sowie in der tierernaehrung
GB2064527B (en) *	1979-12-08	1984-05-02	Nippon Shinyaku Co Ltd	Moranoline derivatives and process for preparation thereof
DE3038901A1 (de) *	1980-10-15	1982-05-06	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von n-substituierten derivaten des 1-desoxynojirimycins
JPS61115093A (ja) *	1984-11-09	1986-06-02	Nippon Shinyaku Co Ltd	モラノリン誘導体の製法
US4634765A (en) *	1984-12-18	1987-01-06	Merrell Dow Pharmaceuticals Inc.	Homodisaccharide hypoglycemic agents
GB2181729B (en) *	1985-10-12	1990-04-04	Nippon Shinyaku Co Ltd	Glucosylmoranoline derivatives and production thereof
DE3737523A1 (de) *	1987-11-05	1989-05-18	Bayer Ag	Verwendung von substituierten hydroxypiperidinen als antivirale mittel

1988
- 1988-06-02 EP EP88401340A patent/EP0344383A1/de not_active Withdrawn
1989
- 1989-04-28 ES ES89401227T patent/ES2081857T3/es not_active Expired - Lifetime
- 1989-04-28 DE DE68924670T patent/DE68924670T2/de not_active Expired - Fee Related
- 1989-04-28 AT AT89401227T patent/ATE129716T1/de not_active IP Right Cessation
- 1989-05-29 AR AR89314032A patent/AR247890A1/es active
- 1989-05-29 ZA ZA894068A patent/ZA894068B/xx unknown
- 1989-05-30 IL IL90463A patent/IL90463A0/xx not_active IP Right Cessation
- 1989-05-30 NZ NZ229337A patent/NZ229337A/en unknown
- 1989-05-30 CA CA000601196A patent/CA1339740C/en not_active Expired - Fee Related
- 1989-05-30 AU AU35801/89A patent/AU608711B2/en not_active Ceased
- 1989-05-31 HU HU892791A patent/HU203559B/hu not_active IP Right Cessation
- 1989-06-01 KR KR1019890007498A patent/KR0155541B1/ko not_active Expired - Fee Related
- 1989-06-01 NO NO892230A patent/NO170023C/no not_active IP Right Cessation
- 1989-06-01 PH PH38729A patent/PH25908A/en unknown
- 1989-06-01 FI FI892682A patent/FI92934C/fi not_active IP Right Cessation
- 1989-06-01 DK DK267489A patent/DK267489A/da not_active Application Discontinuation
- 1989-06-01 CN CN89103723A patent/CN1023803C/zh not_active Expired - Fee Related
- 1989-06-01 PT PT90713A patent/PT90713B/pt not_active IP Right Cessation
- 1989-06-02 JP JP1139401A patent/JP2791419B2/ja not_active Expired - Fee Related
- 1989-06-12 IE IE179889A patent/IE68455B1/en not_active IP Right Cessation
1992
- 1992-02-18 US US07/839,014 patent/US5157116A/en not_active Expired - Fee Related
1995
- 1995-12-08 GR GR950403473T patent/GR3018354T3/el unknown

Also Published As

Publication number	Publication date
FI892682A0 (fi)	1989-06-01
FI892682L (fi)	1989-12-03
FI92934B (fi)	1994-10-14
KR910000776A (ko)	1991-01-30
ATE129716T1 (de)	1995-11-15
IE68455B1 (en)	1996-06-26
NO892230D0 (no)	1989-06-01
CN1023803C (zh)	1994-02-16
NO892230L (no)	1989-12-04
ZA894068B (en)	1990-09-26
CA1339740C (en)	1998-03-17
GR3018354T3 (en)	1996-03-31
HUT50191A (en)	1989-12-28
JPH0225498A (ja)	1990-01-26
JP2791419B2 (ja)	1998-08-27
IL90463A0 (en)	1990-01-18
NO170023B (no)	1992-05-25
AU608711B2 (en)	1991-04-11
PT90713A (pt)	1989-12-29
US5157116A (en)	1992-10-20
AR247890A1 (es)	1995-04-28
IE891798L (en)	1989-12-02
DK267489A (da)	1989-12-03
DK267489D0 (da)	1989-06-01
NZ229337A (en)	1990-12-21
PH25908A (en)	1991-12-19
KR0155541B1 (ko)	1998-10-15
FI92934C (fi)	1995-01-25
ES2081857T3 (es)	1996-03-16
DE68924670D1 (de)	1995-12-07
PT90713B (pt)	1993-09-30
DE68924670T2 (de)	1996-05-23
NO170023C (no)	1992-09-02
CN1040032A (zh)	1990-02-28
AU3580189A (en)	1990-02-01
EP0344383A1 (de)	1989-12-06

Legal Events

Date	Code	Title	Description
2001-02-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
HU203559B (en)	1991-08-28	Process for producing 1-deoxy-nojirimicin derivatives and pharmaceutical compositions containing them as active components
Kraus et al.	1988	A direct synthesis of C-glycosyl compounds
US5504078A (en)	1996-04-02	α-glucosidase inhibitors
Dondoni et al.	1994	Thiazole-based synthesis of formyl C-glycosides
US5464826A (en)	1995-11-07	Method of treating tumors in mammals with 2',2'-difluoronucleosides
EP0285884A2 (de)	1988-10-12	Verfahren zur Herstellung von 2',3'-Dideoxynucleoside
HUT68169A (en)	1995-05-29	Process for producing morphine-6-glucuronide or substituted morphine-6-glucuronide
Skrydstrup et al.	1997	1, 2‐cis‐C‐glycoside synthesis by samarium diiodide‐promoted radical cyclizations
EP0519464B1 (de)	1995-12-20	Nucleosidderivate und deren Herstellung
EP0422975B1 (de)	1994-07-27	Alpha-Glukosidase-Inhibitoren
KR20040031784A (ko)	2004-04-13	Ｌ-리바비린의 제조 방법
JP5550234B2 (ja)	2014-07-16	フラノース誘導体の製造方法
HU198505B (en)	1989-10-30	Process for producing antitumour anthracycline glycosides
WO2007025304A2 (en)	2007-03-01	Process for preparing saccharinic acids and lactones
EP0532668B1 (de)	1995-11-15	Neue alpha-glukosidaseinhibitoren
EP1931693A2 (de)	2008-06-18	Verfahren zur herstellung von gemcitabin und damit in zusammenhang stehenden zwischenprodukten
US5262531A (en)	1993-11-16	Process for preparing 2'-deoxy-β-adenosine
US5126437A (en)	1992-06-30	Aldophosphamide glycosides, a process for their preparation and their use as pharmaceutical active compounds
EP0390674A1 (de)	1990-10-03	Alpha-Glucosidase-Inhibitoren
WO2007070804A2 (en)	2007-06-21	Process for preparing gemcitabine and associated intermediates
JPH0881490A (ja)	1996-03-26	３−ｏ−（３−ｏ−カルバモイルマンノピラノシル）ヘプテノール誘導体、及びマンノグロース誘導体の製造法
IE75889B1 (en)	1997-09-24	Stereo and enantioselective synthesis of tetrahydro-5-substituted-3-methylene-2-furanmethanols
Walczak et al.	1991	Synthesis of 1‐[2, 3‐dideoxy‐3‐(3‐hydroxypropyl)‐d‐pentofuranosyl] thymines
SATO et al.	1989	Synthesis of 2-Substituted Adenine-arabinosides and Related Compounds from 5-Amino-4-cyano-1-(β-D-ribofuranosyl) imidazole
JPH0238595B2 (de)	1990-08-31